Water → HCID 67244239, compound

HRID 2425459Notes

Reaction equation

HRID 2425459 reaction equation
Br[CH2:2][C:3]([NH:5][C@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[NH:24]1[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25]1.O>C(#N)C.C(Cl)(Cl)Cl>[OH:29][CH:26]1[CH2:27][CH2:28][N:24]([CH2:2][C:3]([NH:5][C@H:6]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]2)=[O:4])[CH2:25]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 982104-HydroxypyrrolidineHCID 67243210HCID 67243210, compound

Product 1

HCID 67244239HCID 67244239, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of (S)-3-(2-bromoacetyl)amino-1-(tert-butoxycarbonyl)pyrrolidine (671 mg) prepared in Example 113, Step A and potassium carbonate (604 mg) in acetonitrile (6 ml) was added with 3-pyrrolidinol (190 mg, Tokyo Kasei Kogyo), and the mixture was stirred at room temperature for 22 hours. The reaction mixture was added with water and chloroform, and the organic layer was separated. Further, the aqueous layer was extracted with chloroform, and the combined organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound (531 mg).

Workup

  1. customthe organic layer was separated
  2. extractionFurther, the aqueous layer was extracted with chloroform
  3. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-755cc1f1e931455194ba630a00b66062
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Reaction notes

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